1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide

Waldrep, T. W.; Taylor, H. M.

doi:10.1021/jf60208a047

Cited by 44 publications

(32 citation statements)

References 2 publications

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“…t Range of replicate means. done produces unambiguous visual symptoms that are not similar to those caused by nutrient imbalances or leaf diseases (Waldrep and Taylor, 1978). Once a fturidone layer has been applied to the soil and alfalfa germplasms have been seeded, no specialized equipment and little training are required to distinguish between plants that have active roots in the fturidone-treated zone from those that do not.…”

Section: Discussionmentioning

confidence: 99%

“…Plants absorb fturidone through their shoots and roots (Albritton and Parka, 1978;Rafii and Ashton, 1979), and nearly all species show symptoms of leaf chlorosis, reduced growth, and death after absorption of sufficient amounts, although there are differences in tolerance among species (Albritton and Parka, 1978;Berard et al, 1978;Miller and Carter, 1983). Plant uptake offturidone results in distinctive, easily identified albescence (bleaching) of newly emerging leaves (Waldrep and Taylor, 1978). Fluridone does not leach readily in most mediumand finetextured soils (Banks and Merkle, 1979), because it is adsorbed to clays and, in particular, to organic matter (Weber et al, 1986;Mossier et al, 1993).…”

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confidence: 99%

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Fluridone Reveals Root Elongation Differences among Alfalfa Germplasms

1996

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Alfalfa (Medicago sativa L.) is a deep‐rooted perennial that may be able to remove nitrate from subsoil beneath the rooting zone of annual crops. Alfalfa cultivars with rapid and deep root elongation would be beneficial for reducing future nitrate contamination of ground water supplies. The objectives of this research were to (i) develop a protocol using the herbicide fluridone {1‐methyl‐3‐phenyl‐5‐[3‐(trifluromethyl) penyl]‐4(1H)‐pyridinone} as a marker for indicating alfalfa root penetration in soil, and (ii) determine the variability in rate of geotropic root elongation within and among diverse alfalfa germplasms. Fluridone caused rapid, distinctive bleaching of alfalfa leaves at a rate of 25 mg a.i. kg−1 soil, without being fatal. When transplanted after onset of fluridone symptoms, alfalfa recovered and resumed normal growth and flowering. Alfalfa populations did not differ in sensitivity to fluridone. Decomposition of roots from a fluridone‐treated plant did not cause symptom development in other plants. Individual plants within alfalfa germplasms differed by 56 d in onset of symptoms, indicating a similar difference in root activity at 80 cm depth in soil. Mean geotropic root elongation rate for 12 diverse germplasms ranged from 1.12 to 1.40 cm d−1. Populations selected for unique root morphological traits were significantly faster in geotropic root elongation rate than their nonselected parental populations. Our method permits in situ identification of plants with rapid geotropic root elongation rates within heterogeneous populations and has proven useful in germplasm selection.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Fluridone Reveals Root Elongation Differences among Alfalfa Germplasms

1996

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“…Numerous relevant chemical classes of compounds have now been described (Scheme 17). A common substituent in most of the phytoene desaturase inhibitors is the 3-trifluoromethylphenyl moiety shown in norflurazon (76), [96] which is used for pre-emergence control of annual grasses and broad-leaved weeds, fluridone (77), [97] a selective water herbicide with activity against aquatic plants, and fluorochloridone (78), [98] a herbicide used for pre-and post-emergence control in maize, as well as in cereals and cotton. It is still not known which structural elements are essential to make a phytoene desaturase inhibitor potent at its target site.…”

Section: Inhibitors Of Carotenoid Biosynthesismentioning

confidence: 99%

“…Particularly good activity and cereal selectivity were identified for substitution of the sulfonylaryl moiety with CF 3 and CF 3 O. Exchange of the ortho-COOCH 3 substituent for an ortho-CF 3 O residue in the sulfonylaryl moiety led to flucarbazone sodium (97), [126] a herbicide with excellent activity against grass weeds and several important broadleaf weeds when applied post-emergence to wheat. In field experiments, this product has demonstrated good, consistent activity against wild oat and green foxtail.…”

Section: Sulfonylureasmentioning

confidence: 99%

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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The task of inventing and developing active ingredients with useful biological activities requires a search for novel chemical substructures. This process may trigger the discovery of whole classes of chemicals of potential commercial interest. Similar biological effects can often be achieved by completely different compounds. However, compounds within a given structural family may exhibit quite different biological activities depending on their interactions with different intracellular proteins like enzymes or receptors. By varying the functional groups and structural elements of a lead compound, its interaction with the active site of the target protein, as well as its physicochemical, pharmacokinetic, and dynamic properties can be improved. In this context, the introduction of fluorine into active ingredients has become an important concept in the quest for a modern crop protection product with optimal efficacy, environmental safety, user friendliness, and economic viability. Fluorinated organic compounds represent an important and growing family of commercial agrochemicals. A number of recently developed agrochemical candidates represent novel classes of chemical compounds with new modes of action; several of these compounds contain new fluorinated substituents. However, the complex structure-activity relationships associated with biologically active molecules mean that the introduction of fluorine can lead to either an increase or a decrease in the efficacy of a compound depending on its changed mode of action, physicochemical properties, target interaction, or metabolic susceptibility and transformation. Therefore, it is still difficult to predict the sites in a molecule at which fluorine substitution will result in optimal desired effects.

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“…Fluridone (l-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(lH)-pyridinone) is a fluorinated pyridinone-based aquatic herbicide (Waldrep and Taylor, 1976) available in granular, liquid, and controlled-release fiber formulations (Sanders and Theriot, 1979;Van and Steward, 1985).…”

Section: Fluridonementioning

confidence: 99%

Literature review of the environmental fate of four herbicides applied to surface-water bodies in New Jersey

Gibs¹

1998

Open-File Report

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Four of the most frequently used organic herbicides applied to surface-water bodies in New Jersey are diquat, endothall, fluridone, and glyphosate. These four herbicides are used primarily to control rooted vegetation in lakes, impoundments, and other surface-water bodies with low water velocities. In 1994, the active ingredients in the four herbicides were applied to the surface area of water bodies in New Jersey as follows: diquat, 3,720 pounds (1,688 kilograms) was applied to 2,643 acres (1,070 hectares); endothall, 3,920 pounds (1,778 kilograms) was applied to 408 acres (165 hectares); fluridone, 160 pounds (73 kilograms) was applied to 1,082 acres (438 hectares); and glyphosate, 590 pounds (268 kilograms) was applied to 220 acres (89 hectares). Each of the four organic compounds has different modes of herbicidal action and different behaviors in the aquatic environment, resulting in different application constraints or variables to achieve effective control of nuisance vegetation. The variables include target plant or plants; amount of active ingredient per application; application method and formulation; and season, time of day, and weather conditions required for application. The available body of information concerning the environmental fate and possible modes of transport of diquat, endothall, fluridone, and glyphosate is described, and the sources are listed. This information can be used to determine whether the herbicide is being applied in a manner that is effective, minimizes exposure to the users of the treated water, and prevents unintended changes to the aquatic environment. Environmental fate studies conducted under controlled laboratory conditions, environmental fate and transport studies conducted on site, and numerical simulations of field applications or controlled laboratory studies are included. The literature reviewed in this report was published during 1960-95; literature published during 1980-95 is emphasized.

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1-Methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(1H)-pyridinone, a new herbicide

Cited by 44 publications

References 2 publications

Fluridone Reveals Root Elongation Differences among Alfalfa Germplasms

Fluridone Reveals Root Elongation Differences among Alfalfa Germplasms

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

Literature review of the environmental fate of four herbicides applied to surface-water bodies in New Jersey

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